US5130265A - Process for obtaining a multifunctional, ion-selective-membrane sensor using a siloxanic prepolymer - Google Patents

Process for obtaining a multifunctional, ion-selective-membrane sensor using a siloxanic prepolymer Download PDF

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US5130265A
US5130265A US07/454,512 US45451289A US5130265A US 5130265 A US5130265 A US 5130265A US 45451289 A US45451289 A US 45451289A US 5130265 A US5130265 A US 5130265A
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sub
range
deposition
siloxanic
solution
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Massimo Battilotti
Giuseppina Mazzamurro
Matteo Giongo
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Eni Tecnologie SpA
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Eniricerche SpA
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Assigned to ENIRICERCHE S.P.A. reassignment ENIRICERCHE S.P.A. ASSIGNMENT OF ASSIGNORS INTEREST. Assignors: BATTILOTTI, MASSIMO, GIONGO, MATTEO, MAZZAMURRO, GIUSEPPINA
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    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N27/00—Investigating or analysing materials by the use of electric, electrochemical, or magnetic means
    • G01N27/26—Investigating or analysing materials by the use of electric, electrochemical, or magnetic means by investigating electrochemical variables; by using electrolysis or electrophoresis
    • G01N27/403—Cells and electrode assemblies
    • G01N27/414—Ion-sensitive or chemical field-effect transistors, i.e. ISFETS or CHEMFETS

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  • the present invention relates to a process for obtaining a multifunctional, ion-selective-membrane, sensor (i.e., a "multiprobe").
  • photolithography see. S. Nakamoto, N. Ito, T. Kirigama, J. Kimura: Sensors and Actuators--13, 1988, 165; Y. Hazanato, M. Nakako, M. Maede, J. Shicno: Anal. Chimica Acta, 193, 1987, 87).
  • FIG. 1 is a graphic depiction of a process for production of a multiprobe according to the prior art.
  • FIG. 2 is a graphic depiction of a process for production of a multiprobe according to the present invention, wherein two ion-selective membranes are not in contact with each other.
  • FIG. 3 is an exploded view of a multiprobe according to the invention.
  • FIG. 4 is a microspectrofluorimeter profile of a glass-type substrate obtained according to the present invention.
  • FIG. 5 is microspectrofluorimeter profile of an oxidized and silanized silicon substrate obtained according to the present invention.
  • FIG. 6 is a graphic depiction of a process for production of a multiprobe according to the present invention, wherein two ion-selective membranes are in contact with each other.
  • FIG. 1 a general process of this type is schematically shown, which uses a photoresist.
  • a photoresist (F) is applied by means of a spinner [FIG. 1(b)].
  • the membrane (P) is then deposited by means of a spinner [FIG. 1(e)], and a second photochemical treatment [FIG. 1(f)] is carried out, which second photochemical treatment is followed by a lift-off process, or by a process of washing with solvents, and by a thermal treatment, with the ion-selective membrane (A) being obtained [FIG. 1(g)].
  • the chemical-physical characteristics of the polymeric material from which the membrane is made are very similar to those of a photoresist, but with the possibility of operating in white light and not only in the dark, or in yellow light, as required by the use of the same photoresist;
  • the polymeric material which is obtained is bonded by means of chemical bonds to the silanized surface of the gate of the FET with reactive groups, whilst in case of use of membranes as photoresist, such chemical bonds are not formed;
  • the number of process steps is lower than as needed when a photoresist is used.
  • the process according to the present invention for obtaining a multifunctional, ion-selective-membrane, sensor which sensor is essentially constituted by a device based on semiconductors of MOS (Metal Oxide Semiconductor) type or of ISFET type (ISFET is an acronym standing for In Selective Field Effect Transistor), containing silicon oxide on its surface, and having two or more gates, and by two or more ioncphores, different from one another, with each one of said ionophores being entrapped inside a polymeric organic matrix based on a polymer obtained by means of the reaction between a polymerized olefin, the monomer of which has the formula: ##STR1## wherein: Z I is equal to ##STR2## or to
  • r is an integer which can have values of from 1 to 10;
  • R V can be either H or CH 3 , with the value of CH 3 being excluded when Z I is equal to (CH 2 ) r ,
  • n is an integer which can have values comprised within the range of from 1 to 20,000;
  • s is an integer which can have values comprised within the range of from 1 to 20,
  • R VI is equal to: ##STR4## wherein: t is an integer which can have values comprised within the range of from 1 to 10, and
  • Z can be either --NH-- or --O--, with the value of --NH-- being excluded when R VI is equal to:
  • n I is an integer which can have a value comprised within the range of from 100 to 10,000, with a suitable mask being used, which allows the exposure to UV light to take place on one gate only;
  • thermal treatment "thermal curing"
  • the polysiloxanic matrix can be preferably selected from among the organosilanes of general formula ##STR5## wherein R II , R III , R IV , which can be either equal to, or different from, one another, are alkyl or alkoxy groups containing from 1 to 10 carbon atoms, and
  • R I is equal to
  • X is CH 2 or a monocondensed or polycondensed aromatic group or NH or O
  • p and q which can be either equal to, or different from, each other, are integers which can have values comprised within the range of from 0 to 10, with the value of zero being excluded when X is either NH or O,
  • Y is --NH 2 or --OH or --SH.
  • the structure obtained from the polysiloxanic matrix from the polymeric organic matrix and from the silicon oxide existing on the surface of the MOS or ISFET device can be schematically represented as follows: ##STR6##
  • AEAPS aminoethylaminopropyltrimethoxysilane
  • AEAMPS aminoethylaminomethylphenetyltrimethoxysilane
  • 3-aminopropyltriethoxysilane for exemplifying purposes, aminoethylaminopropyltrimethoxysilane (AEAPS) or aminoethylaminomethylphenetyltrimethoxysilane (AEAMPS) or 3-aminopropyltriethoxysilane can be used.
  • organic molecules with an open structure such as, e.g., of the type of ETH 227, ETH 1001, ETH 1644, and so forth
  • a cyclic structure such as of the type, e.g., of Valinomycin, the crown-ethers, the cryptands, and so forth
  • the device of MOS type besides the presence of silicon oxide and, possibly, silicon nitride, on its surface, should contain in its portion under the same silicon a layer of aluminum or gold, deposited by evaporation.
  • the polymeric organic matrix hydroxyethylmethacrylato and a compound obtained by means of the reaction of 2,4-toluene-diisocyanate and triethyleneglycol or triethanolamine, can be used.
  • the depositions of the siloxanic prepolymer and of the solution containing the constitutents of the membrane and the ionophore can be carried out by means of the so-said "spin-on" techniques, i.e., by using a rotary-disk equipment.
  • the excess of so-deposited solution is removed by centrifugation, owing to the revolutionary movement of the disk.
  • the solvent of the solution evaporates and the compound(s) in question polymerize(s) and react(s) under the thermal and photochemical effect.
  • the thermal treatments of the siloxanic prepolymer and of the solution containing the components of the selective membrane deposited on the polysiloxanic layer are preferably carried out at a temperature comprised within the range of from 40° to 200° C., and preferably comprised within the range of from 80° to 150° C.
  • the photochemical treatment by means of the use of UV light, is carried out, e.g., by means of a mercury-vapour lamp (type HBO 100/W2).
  • the deposited thickness of siloxanic prepolymer should be comprised within the range of from 0.1 to 10 ⁇ m, and should be preferably comprised within the range of from 0.5 to 3 ⁇ m, and the deposited thickness of the membrane-containing solution should be comprised within the range of from 0.1 to 100 m, and preferably comprised within the range of from 10 ⁇ to 30 ⁇ m.
  • the revolution speed (revolutions per minute, rpm) at which the depositions by means of spin-on devices are carried out should be comprised within the range of from 500 to 6000, and preferably of from 3500 to 5500, rpm.
  • the deposition of the siloxanic prepolymer on substrates of silicon or of silicon oxide of devices of MOS or ISFET type can be carried out by plasma-deposition, preferably under the following conditions:
  • discharge pressure comprised within the range of from 0.1 to 1 torr;
  • the purpose is of directly obtaining on a semiconductor device functionalized with reactive organosilanes, regions coated by selective membranes, and regions without said membranes.
  • Example 1 llustrates the process for depositing two ion-selective membranes not into contact with each other, and Example 2 illustrates the process for depositing two membranes into contact with each other along one side.
  • Example 2 The advantage of the process of Example 2 is that during the step of preparation of the sensor, such a process does not require the use of a sealant between the two membranes.
  • Example 1 is schematically illustrated in the flow diagram of FIG. 2.
  • the starting substrate is a FET device (i.e., a "Field Effect Transistor").
  • the starting solution is constituted by:
  • the deposition is carried out by means of a rotary-disk device at 5000 rpm for 30 seconds (spin-coating).
  • a precuring of siloxane at 150° C. for 20 minutes can be optionally carried out.
  • FIG. 1(a) the silanized FET (F) is shown, which has two gates (the source and the drain of each gate are represented as small rectangles of black colour).
  • the solution is prepared, which contains the diisocyanate-based compound, obtained as follows:
  • the deposition is carried out by means of a spin-coating technique, by operating at 5000 rpm for 30 seconds. The deposition process is repeated twice.
  • the device is exposed to the effect of UV light for a time of 5 minutes, with the UV lamp being kept at a distance of about 25 cm from the samples. In this way, the complete polymerization of methacrylate is only obtained in the region left uncovered by the mask.
  • the device is subsequently submitted to a treatment of thermal type at 110° C. for a time of 8 hours.
  • the complete condensation is obtained between the --OH groups of the methacrylate and of the aminosilane, with the --NCO groups of the compound obtained by means of the reaction of toluenediisocyanate with triethyleneglycol.
  • the complete polymerization of the pre-hydrolised organosilane, and the reaction of the alkoxide groups with the --SiOH groups of sil con oxide take place.
  • the solution is prepared, which contains the diisocyanate-tased compound, obtained as follows:
  • an ionophore different from Valinomycin such as, e.g., Nonactin, selective for NH 4 + and 1% of 2,2-diethoxyacetophenone, to be used as the photoinitiator of methacrylate polymerization, are added.
  • an ionophore different from Valinomycin such as, e.g., Nonactin, selective for NH 4 + and 1% of 2,2-diethoxyacetophenone, to be used as the photoinitiator of methacrylate polymerization
  • the deposition is carried out by means of a spin-coating technique, by operating at 5000 rpm for 30 seconds. The deposition process is repeated twice.
  • the device is exposed to the effect of UV light for a time of 5 minutes, with the lamp being kept at a distance of about 25 cm from the samples. In this way, the complete polymerization of methacrylate is obtained.
  • the device is subsequently submitted to a second treatment of thermal type at 110° C. for a time of 8 hours.
  • the complete condensation is obtained between the --OH groups of the methacrylate and of the aminosilane, with the --NCO groups of the compound obtained by means of the reaction of toluenediisocyanate with triethyleneglycol.
  • the complete polymerization of the prehydrolised organosilane, and the reaction of the alkoxide groups with the --SiOH groups of silicon oxide take place [FIG. 2(g)].
  • FIG. 3 shows the result which can be obtained on a dual-gate FET, wherein:
  • FIG. 4 shows the result obtained according to this process on a silanized substrate of glass type.
  • FIG. 5 shows the result obtained according to this process on an oxidated and silanized silicon substrate.
  • FIGS. 4 and 5 The profile shown in FIGS. 4 and 5 was obtained by exploiting the effect of fluorescence of the polymeric material, as recorded by means of a microspectrofluorimeter.
  • a and B are, as said, polymeric membranes chemically bonded to the device, with selectivities for different ions, in that they contain different ionophores.
  • Example 1 The same procedure as of Example 1 is followed, as schematically shown in the flow diagram of FIG. 6; the end result is that two membranes with different selectivity are produced, partially superimposed to each other on one side only.
  • FIG. 6 The flow diagram of FIG. 6 is analogous to that of FIG. 3; the only variations are the opening is wider [FIG. 3(c), (f)] and the resulting overlapping [FIG. 3(h)].

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  • Investigating Or Analyzing Materials By The Use Of Fluid Adsorption Or Reactions (AREA)
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US07/454,512 1988-12-23 1989-12-21 Process for obtaining a multifunctional, ion-selective-membrane sensor using a siloxanic prepolymer Expired - Fee Related US5130265A (en)

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IT23105A/88 1988-12-23
IT8823105A IT1228120B (it) 1988-12-23 1988-12-23 Procedimento per ottenere un sensore multifunzionale a membrana ionoselettiva

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Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5854863A (en) * 1996-03-15 1998-12-29 Erb; Judith Surface treatment and light injection method and apparatus
DE19829413A1 (de) * 1998-07-01 2000-01-13 Michael Glaeser Verfahren zur Herstellung von ionensensitiven und Membrane darstellende Schichten auf einem Träger und Verwendung mindestens einer Drucktechnik zur Herstellung von Anordnungen zur qualitativen und/oder quantitativen Bestimmung von Ionen oder Stoffen in Lösungen
WO2001057920A1 (fr) * 2000-02-01 2001-08-09 Analog Devices, Inc. Procede de traitement sur tranche destine a reduire le frottement statique et a passiver les surfaces micro-usinees et composes utilises a cet effet
US6387724B1 (en) 1999-02-26 2002-05-14 Dynamics Research Corporation Method of fabricating silicon-on-insulator sensor having silicon oxide sensing surface
US6525554B2 (en) 2000-07-20 2003-02-25 National Yunlin University Of Science And Technology Method and apparatus for measuring temperature parameters of an ISFET using hydrogenated amorphous silicon as a sensing film
US20050221594A1 (en) * 2004-03-31 2005-10-06 Jung-Chuan Chou ISFET with TiO2 sensing film
US7009376B2 (en) 2002-05-20 2006-03-07 National Yunlin University Of Science And Technology SnO2 ISFET device, manufacturing method, and methods and apparatus for use thereof
US20060220092A1 (en) * 2005-04-04 2006-10-05 National Yunlin University Of Science And Technology Titanium oxide extended gate field effect transistor
US20070065582A1 (en) * 2005-09-21 2007-03-22 Ford Global Technologies, Llc Method of coating a substrate for adhesive bonding
US20070095663A1 (en) * 2005-11-01 2007-05-03 National Yunlin University Of Science And Technology Preparation of a PH sensor, the prepared PH sensor, system comprising the same and measurement using the system
US20070184201A1 (en) * 2003-06-18 2007-08-09 Ford Global Technologies Llc Environmentally friendly reactive fixture to allow localized surface engineering for improved adhesion to coated and non-coated substrates
US20080003436A1 (en) * 2006-06-28 2008-01-03 Ford Global Technologies, Llc Method of treating substrates for bonding
US20080067081A1 (en) * 2006-09-19 2008-03-20 National Yunlin University Of Science And Technology pH measurement system and method for reducing time-drift effects thereof
US20100051916A1 (en) * 2000-10-04 2010-03-04 Cambridge University Technical Services Limited Method for forming an electronic device in multi-layer structure
US20100151236A1 (en) * 2008-12-11 2010-06-17 Ford Global Technologies, Llc Surface treatment for polymeric part adhesion

Families Citing this family (3)

* Cited by examiner, † Cited by third party
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FR2666930B1 (fr) * 1990-09-14 1992-12-18 Lyon Ecole Centrale Procede et realisation d'une surface-grille d'un capteur electrochimique integre, constitue d'un transistor a effet de champ et sensible aux especes alcalino-terreuses et capteur obtenu.
CH683874A5 (fr) * 1990-10-02 1994-05-31 Suisse Electronique Microtech Dispositif semi-conducteur comportant une membrane possédant une sensibilité sélective aux ions et procédé de réalisation de la membrane.
ES2114436B1 (es) * 1995-03-31 1999-04-01 Consejo Superior Investigacion Encapsulacion automatizada de sensores quimicos de estado solido empleando fotopolimeros que contienen resinas epoxi y poliuretanos acrilatos.

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US4236987A (en) * 1977-11-14 1980-12-02 Dr. E. Fresenius Chemisch Pharmazeutische Industrie Kg Apparatebau Kg Electrode having membrane with ion selective properties
US4269682A (en) * 1977-12-12 1981-05-26 Kuraray Co., Ltd. Reference electrode of insulated gate field effect transistor
US4505799A (en) * 1983-12-08 1985-03-19 General Signal Corporation ISFET sensor and method of manufacture
US4735702A (en) * 1984-03-22 1988-04-05 Stichting Centrum Voor Micro-Electronica Twente Method of producing an ISFET and same ISFET
US4874499A (en) * 1988-05-23 1989-10-17 Massachusetts Institute Of Technology Electrochemical microsensors and method of making such sensors
US4878015A (en) * 1985-07-23 1989-10-31 Fraunhofer-Gesellschaft Zur Forderung Der Angewandten Forschung E.V. Sensors for selectively determining liquid-phase or gas-phase components using a heteropolysiloxane sensitive layer

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IT1198226B (it) * 1986-12-04 1988-12-21 Eniricerche Spa Dispositivo sensibile agli ioni
IT1222121B (it) * 1987-07-24 1990-08-31 Eniricerche Spa Sensore per ioni contenente una membrana organica selettiva

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US4218298A (en) * 1977-11-04 1980-08-19 Kuraray Co., Ltd. Selective chemical sensitive FET transducer
US4236987A (en) * 1977-11-14 1980-12-02 Dr. E. Fresenius Chemisch Pharmazeutische Industrie Kg Apparatebau Kg Electrode having membrane with ion selective properties
US4269682A (en) * 1977-12-12 1981-05-26 Kuraray Co., Ltd. Reference electrode of insulated gate field effect transistor
US4505799A (en) * 1983-12-08 1985-03-19 General Signal Corporation ISFET sensor and method of manufacture
US4735702A (en) * 1984-03-22 1988-04-05 Stichting Centrum Voor Micro-Electronica Twente Method of producing an ISFET and same ISFET
US4878015A (en) * 1985-07-23 1989-10-31 Fraunhofer-Gesellschaft Zur Forderung Der Angewandten Forschung E.V. Sensors for selectively determining liquid-phase or gas-phase components using a heteropolysiloxane sensitive layer
US4874499A (en) * 1988-05-23 1989-10-17 Massachusetts Institute Of Technology Electrochemical microsensors and method of making such sensors

Cited By (29)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5952035A (en) * 1996-03-15 1999-09-14 Ia, Inc. Surface treatment and light injection method and apparatus
US5854863A (en) * 1996-03-15 1998-12-29 Erb; Judith Surface treatment and light injection method and apparatus
DE19829413A1 (de) * 1998-07-01 2000-01-13 Michael Glaeser Verfahren zur Herstellung von ionensensitiven und Membrane darstellende Schichten auf einem Träger und Verwendung mindestens einer Drucktechnik zur Herstellung von Anordnungen zur qualitativen und/oder quantitativen Bestimmung von Ionen oder Stoffen in Lösungen
US6387724B1 (en) 1999-02-26 2002-05-14 Dynamics Research Corporation Method of fabricating silicon-on-insulator sensor having silicon oxide sensing surface
US6674140B2 (en) 2000-02-01 2004-01-06 Analog Devices, Inc. Process for wafer level treatment to reduce stiction and passivate micromachined surfaces and compounds used therefor
CN1314086C (zh) * 2000-02-01 2007-05-02 模拟装置公司 具有抗静摩擦特性的芯片、微机电装置及其制造方法
US20030211650A1 (en) * 2000-02-01 2003-11-13 Analog Devices, Inc. Process for wafer level treatment to reduce stiction and passivate micromachined surfaces and compounds used therefor
US7364942B2 (en) 2000-02-01 2008-04-29 Analog Devices, Inc. Process for wafer level treatment to reduce stiction and passivate micromachined surfaces and compounds used therefor
WO2001057920A1 (fr) * 2000-02-01 2001-08-09 Analog Devices, Inc. Procede de traitement sur tranche destine a reduire le frottement statique et a passiver les surfaces micro-usinees et composes utilises a cet effet
US20070196945A1 (en) * 2000-02-01 2007-08-23 Analog Devices, Inc. Process for wafer level treatment to reduce stiction and passivate micromachined surfaces and compounds used therefor
US7220614B2 (en) 2000-02-01 2007-05-22 Analog Devices, Inc. Process for wafer level treatment to reduce stiction and passivate micromachined surfaces and compounds used therefor
US6573741B2 (en) 2000-07-20 2003-06-03 Univ Nat Yunlin Sci & Tech Apparatus for measuring temperature parameters of an ISFET using hydrogenated amorphous as a sensing film
US6525554B2 (en) 2000-07-20 2003-02-25 National Yunlin University Of Science And Technology Method and apparatus for measuring temperature parameters of an ISFET using hydrogenated amorphous silicon as a sensing film
US20100051916A1 (en) * 2000-10-04 2010-03-04 Cambridge University Technical Services Limited Method for forming an electronic device in multi-layer structure
US7009376B2 (en) 2002-05-20 2006-03-07 National Yunlin University Of Science And Technology SnO2 ISFET device, manufacturing method, and methods and apparatus for use thereof
US8586149B2 (en) 2003-06-18 2013-11-19 Ford Global Technologies, Llc Environmentally friendly reactive fixture to allow localized surface engineering for improved adhesion to coated and non-coated substrates
US20070184201A1 (en) * 2003-06-18 2007-08-09 Ford Global Technologies Llc Environmentally friendly reactive fixture to allow localized surface engineering for improved adhesion to coated and non-coated substrates
US20050221594A1 (en) * 2004-03-31 2005-10-06 Jung-Chuan Chou ISFET with TiO2 sensing film
US20060220092A1 (en) * 2005-04-04 2006-10-05 National Yunlin University Of Science And Technology Titanium oxide extended gate field effect transistor
US7517561B2 (en) * 2005-09-21 2009-04-14 Ford Global Technologies, Llc Method of coating a substrate for adhesive bonding
US20090155604A1 (en) * 2005-09-21 2009-06-18 Ford Global Technologies, Llc Method of coating a substrate for adhesive bonding
US8048530B2 (en) 2005-09-21 2011-11-01 Ford Global Technologies, Llc Method of coating a substrate for adhesive bonding
US20070065582A1 (en) * 2005-09-21 2007-03-22 Ford Global Technologies, Llc Method of coating a substrate for adhesive bonding
US20070095663A1 (en) * 2005-11-01 2007-05-03 National Yunlin University Of Science And Technology Preparation of a PH sensor, the prepared PH sensor, system comprising the same and measurement using the system
US20080003436A1 (en) * 2006-06-28 2008-01-03 Ford Global Technologies, Llc Method of treating substrates for bonding
US7744984B2 (en) 2006-06-28 2010-06-29 Ford Global Technologies, Llc Method of treating substrates for bonding
US20080067081A1 (en) * 2006-09-19 2008-03-20 National Yunlin University Of Science And Technology pH measurement system and method for reducing time-drift effects thereof
US7820029B2 (en) 2006-09-19 2010-10-26 National Yunlin University Of Science And Technology pH measurement system and method for reducing time-drift effects thereof
US20100151236A1 (en) * 2008-12-11 2010-06-17 Ford Global Technologies, Llc Surface treatment for polymeric part adhesion

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EP0375070A1 (fr) 1990-06-27
EP0375070B1 (fr) 1993-03-31
IT1228120B (it) 1991-05-28
IT8823105A0 (it) 1988-12-23
ES2040989T3 (es) 1993-11-01
ATE87740T1 (de) 1993-04-15
DE68905784D1 (de) 1993-05-06
DE68905784T2 (de) 1993-10-28

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